Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Intramolecular Cascade Lactone Cyclization of Dicoumarol Derivatives Promoted by Tributyltin Chloride

Author(s): Sadia Rehman, Muhammad Ikram and Fazle Subhan

Volume 11 , Issue 3 , 2014

Page: [215 - 219] Pages: 5

DOI: 10.2174/1570178610666131210233841

Price: $65

Abstract

Dicoumarols, derived from aldehydes with ortho hydroxy substitution (5 and 7), were successfully cyclized by Sn(n-Bu)3Cl in THF as a reaction medium. Catalytic cycle reveals the formation of HO-Sn-O=C cyclic intermediate which is rearranged and isomerized to the cyclic lactone. N-butane was released by Sn(n-Bu)3Cl leaving behind Sn(n- Bu)2(OH)Cl keeping the catalytic route continued unless the two butane attached to tin were also consumed. The products produced were characterized using 1H, 13C{1H}-NMR, high resolution EI-MS, IR and elemental analyses. Single crystals of 6 were grown in P1 space group from concentration in THF and structurally studied using X-ray diffraction analysis. All the spectroscopic and analytical studies supported the formation of the cyclized products.

Keywords: Sn(n-Bu)3Cl, dicoumarol, intramolecular cyclization, single crystal study, lactone.


Rights & Permissions Print Export Cite as
© 2022 Bentham Science Publishers | Privacy Policy